(2Z)-3-Amino-2-butenenitrile → N-[2-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)furo[3,2-c]pyridin-4-yl]benzamide

HRID 1910666Notes

Reaction equation

[CH:1]([C:3]1[O:11][C:10]2[CH:9]=[CH:8][N:7]=[C:6]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:5]=2[CH:4]=1)=O.[NH2:21]/[C:22](/[CH3:26])=[CH:23]\[C:24]#[N:25]>C(O)(=O)C>[C:24]([C:23]1[CH:1]([C:3]2[O:11][C:10]3[CH:9]=[CH:8][N:7]=[C:6]([NH:12][C:13](=[O:20])[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:5]=3[CH:4]=2)[C:5]([C:6]#[N:7])=[C:4]([CH3:3])[NH:21][C:22]=1[CH3:26])#[N:25]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 69 mg (0.260 mmol) N-(2-formylfuro[3,2-c]pyridin-4-yl)benzamide (Example 3A) and 43 mg (0.52 mmol) (2Z)-3-aminobut-2-enenitrile in acetic acid (4.5 ml) was stirred for 45 min at 110° C. Upon cooling, the reaction mixture was concentrated under reduced pressure, and the residue was treated with ethyl acetate and saturated aq. sodium carbonate solution. The organic layer was separated, washed with brine and water, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound (45 mg, 43% of th.) as a pale yellow solid.

Workup

temperatureUpon cooling
concentrationthe reaction mixture was concentrated under reduced pressure
additionthe residue was treated with ethyl acetate and saturated aq. sodium carbonate solution
customThe organic layer was separated
washwashed with brine and water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-00a340f924b24dada1aeebaa31fbceaf
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604028B2

Reaction notes

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